Chemistry of heterocyclic compounds. 124. Mono-.alpha.-functionalization of 2,9-dimethyl-1,10-phenanthroline

Newkome, George R.; Theriot, Kevin J.; Gupta, Vinod K.; Fronczek, Frank R.; Baker, Gregory R.

doi:10.1021/jo00268a055

Cited by 49 publications

(44 citation statements)

References 1 publication

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“…Compound 45 was esterified with MeOH/H,SO, (4 46), and after reduction with NaBH, in EtOH, diol47 was transformed with PBr, into bis(bromomethy1) derivative 48 without delay, because 47 has a tendency to decompose into an insoluble material. The same phenomenon was also reported by Newkome et al for 9-methyl-l,l0-phenanthroline-2-methanol [23]. The coupling of 48 to di(tert-butyl) iminobis(acetate) and the hydrolysis of ester 49 to the target tetraacetic acid 50 were performed as usually [ 1 11.…”

Section: I)supporting

confidence: 60%

Development of Luminescent Europium(III) and Terbium(III) chelates of 2,2′:6′,2″‐ terpyridine derivatives for protein labelling

Mukkala

Helenius

Hemmilä

et al. 1993

Helvetica Chimica Acta

207

123

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The synthesis and luminescence properties are reported for 20 different chelates composed of 2,2':6',2"-terpyridine as the energy-absorbing and donating group, Eu"' and Tb"' as the emitting ions, methylenenitrilo(acetic acids) as the stable chelate-forming moieties, and isothiocyanato or (4,6-dichloro-1,3,5-triazin-2-yl)amino groups as the activated moieties for coupling to biomolecules.Introduction. -Time-resolved fluorometry combined with long-lifetime emitting lanthanide chelate labels provides an excellent way of creating highly sensitive label technologies for bioaffinity assays [ 11. A technology based on dissociative fluorescence enhancement [2], Devia@, has gained wide applications in the field of clinical diagnostics in immunoassays [3] and recently also in DNA hybridization assays [4]. In spite of the high sensitivity obtained, the Devia-type of technology is not suited for all applications, such as fluorescence imaging, immunohistochemistry, or in situ hybridization, because after ion dissociation it does not produce spatial information. To use luminescent lanthanide chelates also in in situ assays, new chelate labels need to be developed combining

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Section: I)supporting

confidence: 60%

Development of Luminescent Europium(III) and Terbium(III) chelates of 2,2′:6′,2″‐ terpyridine derivatives for protein labelling

Mukkala

Helenius

Hemmilä

et al. 1993

Helvetica Chimica Acta

207

123

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“…The 2-halomethyl-9-methyl- 17 lines18 were synthesized as described. All other neocuproine derivatives were synthesized as described in the previous section.…”

Section: Preparation Of Neocuproine-cuprous Complexesmentioning

confidence: 99%

“…(lanes 13-15), and bathocuproine disulfonate (BS) (lanes [16][17][18]. The upper panel corresponds to a dark exposure to show the DNA integration (strand transfer) products.…”

Section: Reversibility Of Integrase Inhibitionmentioning

confidence: 99%

Inhibition of Human Immunodeficiency Virus Type 1 Integrase by a Hydrophobic Cation: The Phenanthroline-Cuprous Complex

Mazumder¹,

Gupta²,

Perrin³

et al. 1995

AIDS Research and Human Retroviruses

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The human immunodeficiency virus type 1 integrase (HIV-1 integrase) is required for integration of a double-stranded DNA copy of the viral RNA genome into a host chromosome and for HIV replication. We have examined the effects of 2:1 1,10-phenanthroline-cuprous complexes on purified HIV-1 integrase. Although the uncomplexed phenanthrolines are not active below 100 microM, four of the cuprous complexes (neocuproine, 4-phenyl neocuproine, 2,3,4,7,8,9-hexamethyl phenanthroline, and 2,3,4,7,8-pentamethyl phenanthroline) have a 50% inhibitory concentration (IC50) for integration ranging between 1 and 10 microM. Disintegration is also inhibited by these phenanthroline-cuprous complexes at slightly higher concentrations (between 10 and 40 microM). Dialysis experiments showed that the inhibition is reversible and kinetic analyses revealed that the mode of inhibition by these cuprous complexes appears to be noncompetitive with respect to the substrate DNA. Consistent with these findings, binding assays demonstrate that, although these complexes can inhibit binding to DNA at high concentrations, they do not inhibit binding of integrase to the DNA substrate at their IC50 values. Because these complexes do not bind to B-DNA below 50 microM, inhibition via binding to a specific region on the enzyme was examined. Using deletion mutants of integrase, it was determined that neither the amino-terminal (zinc finger) nor the carboxy-terminal (DNA-binding) integrase domain is required for inhibition by the phenanthroline-cuprous complexes. Therefore, inhibition via binding to the enzyme catalytic core or to the interface between the enzyme and a noncanonical DNA structure generated during the enzymatic reaction is the probable mechanism. These results suggest the utility of neocuproine-cuprous complexes in developing inhibitors of HIV-1 integrase as well as probes for drug-binding sites and enzymatic reaction mechanism.

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“…Synthesis of 2-methyl-9-(3,5-dimethylpyrazolylmethyl)-1,10-phenanthroline (L)-2-methyl-9-chloromethyl-1,10-phenanthroline [16] (0.120 g, 0.05 mmol) was dissolved in 50 ml of benzene/CH 2 Cl 2 solution (1/1 v/v) with 3,5-dimethylpyrazole (0.096 g, 1.0 mmol). To this solution were added 20 mL of a 40% solution of NaOH and 0.25 mL of a 40% tetrabutylammonium hydroxide solution.…”

Section: Preparationsmentioning

confidence: 99%

“…The starting material (2,9-dimethyl-1,10-phenanthroline) was converted to its mono-chlorinated form in four-steps, [16] followed by phase transfer coupling to 3,5-dimethylpyrazole to afford L. The Cu(II) (1) and Cu(I) (2) complexes were synthesized by equimolar addition of either Cu(CF 3 SO 3 ) 2 [17] or [Cu(CH 3 CN) 4 ]CF 3 SO 3 [18], respectively, to a solution of L. While the red Cu(I) complex (2) is stable as a solid in air, the complex is air-sensitive in a CH 3 CN solution, and undergoes complete oxidation to a green Cu(II) species in ca. 60 min at RT.…”

Section: Synthesismentioning

confidence: 99%

Synthesis, characterization and copper chemistry of a non-symmetric phenanthroline ligand: 2-Methyl-9-(3,5-dimethyl-N-pyrazolylmethyl)-1,10-phenanthroline

Masood

Storr

Stack

2008

Inorganica Chimica Acta

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The synthesis of an unsymmetrical phenanthroline based ligand, 2-methyl-9-(3,5-dimethylpyrazolylmethyl)-1,10-phenanthroline (L), and its cupric [Cu(II)] (1) and cuprous [Cu(I)] (2) complexes, are reported. The X-ray structures of each of these Cu complexes show distinct changes in coordination environments consistent with the geometrical preferences of the two oxidation states. In the solid state the Cu(II) complex (1) adopts a geometry best described as trigonal bipyramidal, while the Cu(I) complex (2) consists of a single dicationic dimer in which the ligand bridges between two copper ions, separated by 4.26 Å. The two Cu(I) coordination sites differ in 2 with one copper center complexed in a trigonal planar geometry and the other copper in a distorted tetrahedral environment; the latter coordination results from an additional CH 3 CN ligand. Complex 1 exhibits a reversible redox process at −0.34 V vs. Fc/Fc + in CH 3 CN, attributable to the Cu 2+ / Cu + couple, while the dimeric Cu(I) complex (2) is resistant to oxidation on the CV timescale. Over minutes however, complex 1 does oxidize in the presence of dioxygen to 2 in CH 3 CN.

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Chemistry of heterocyclic compounds. 124. Mono-.alpha.-functionalization of 2,9-dimethyl-1,10-phenanthroline

Cited by 49 publications

References 1 publication

Development of Luminescent Europium(III) and Terbium(III) chelates of 2,2′:6′,2″‐ terpyridine derivatives for protein labelling

Development of Luminescent Europium(III) and Terbium(III) chelates of 2,2′:6′,2″‐ terpyridine derivatives for protein labelling

Inhibition of Human Immunodeficiency Virus Type 1 Integrase by a Hydrophobic Cation: The Phenanthroline-Cuprous Complex

Synthesis, characterization and copper chemistry of a non-symmetric phenanthroline ligand: 2-Methyl-9-(3,5-dimethyl-N-pyrazolylmethyl)-1,10-phenanthroline

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